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Synlett 2010(15): 2251-2256  
DOI: 10.1055/s-0030-1258038
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Synthesis of Novel Acyclo-C-Nucleoside Analogues from l-Rhamnose via Variants of Bohlmann-Rahtz Reaction

Srinivas Kantevari*, Siddamal Reddy Putapatri
Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad 500007, India
e-Mail: kantevari@yahoo.com; e-Mail: kantevari@gmail.com;
Further Information

Publication History

Received 9 June 2010
Publication Date:
12 August 2010 (online)

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Abstract

Synthesis of a series of novel acyclo-C-nucleoside analogues bearing substituted pyridines, dihydro-6H-quinolin-5-ones, dihydro-5H-cyclopentapyridin-5-one, tetrahydrocyclohepta[b] pyr­idine-5-one, and azafluorinone has been achieved in very good yields, through CeCl3˙7H2O-NaI-catalyzed one-pot condensation of a variant of the Bohlmann-Rahtz reaction using β-enaminones derived from l-rhamnose, acyclic and cyclic 1,3-dicarbonyls, and ammonium acetate. Ready availability of reactive β-enaminones, use of a cerium catalyst, and shorter reaction times are the advantages of this protocol over previous methodology. A plausible mechanism invoking cerium-catalyzed sequential Michael addition-cyclode­hydration-elimination reactions is also presented.

Key words

Bohlmann-Rahtz reaction - acyclo-C-nucleosides - CeCl3˙7H2O-NaI - one-pot condensation - β-enaminone - l-rhamnose - heterocycles

    References and Notes

  • 1a Wellington KW. Benner SA. Nucleosides, Nucleotides Nucleic Acids  2006,  25:  1309 
    Search in Google Scholar
  • 1b Wu QP. Simons C. Synthesis  2004,  1533 
  • 1c Nasr AZ. Nucleosides, Nucleotides Nucleic Acids  2004,  23:  1825 
    Search in Google Scholar
  • 1d Belkadi M. Othman AA. Trends Appl. Sci. Res.  2011,  6:  17 
    Search in Google Scholar
  • 2a Alonso-Cruz CR. Freire R. Rodriguez MS. Suarez E. Synlett  2007,  2723 
  • 2b Otero I. Methling K. Feist H. Michalik M. Quincoces J. Reinke H. Peseke K.
    J. Carbohydr. Chem.  2005,  24:  809 
    Search in Google Scholar
  • 2c Montero A. Feist H. Michalik M. Quincoces J. Peseke K. J. Carbohydr. Chem.  2002,  21:  305 
    Search in Google Scholar
  • 2d Sagar R. Park SB. J. Org. Chem.  2008,  73:  3270 
    Search in Google Scholar
  • 2e Montero A. Feist H. Michalik M. Quincoces J. Peseke K. Synthesis  2002,  664 
  • For indolizidines, see:
  • 3a Bonanni M. Marradi M. Cardona F. Cicchi S. Goti A. Beilstein J. Org. Chem.  2007,  3:  44 
    Search in Google Scholar
  • For imidazoles, see:
  • 3b Wu W, Yan J, and Zhang H. inventors; WO  2008/128041. 
  • For benzimidazoles, see:
  • 3c Sallam MAE. Waagen V. Anthonsen T. Carbohydr. Res.  2008,  343:  388 
    Search in Google Scholar
  • For nitrones, see:
  • 3d Fischer R. Druckova A. Fisera L. Hametner C. ARKIVOC  2002,  (viii):  80 
    Search in Google Scholar
  • For piperidines, see:
  • 3e Boutefnouchet S. Moldvai I. Gacs-Baitz E. Bello C. Vogel P. Eur. J. Org. Chem.  2007,  3028 
  • For other carbohybrids, see:
  • 3f Yadav LDS. Rai A. Rai VK. Awasthi C. Synlett  2008,  529 
  • 3g Irmak M. Lahnert T. Boysen MMK. Tetrahedron Lett.  2007,  48:  7890 
    Search in Google Scholar
  • 3h Roy AD. Subramanian A. Mukhopadhyay B. Roy R. Tetrahedron Lett.  2006,  47:  6857 
    Search in Google Scholar
  • 4a Le GT. Abbenante G. Becker B. Grathwohl G. Halliday J. Tometzki G. Zuegg J. Meutermans W. Drug Discovery Today  2003,  8:  701 
    Search in Google Scholar
  • 4b Rudloff I. Michalik M. Montero A. Peseke K. Synthesis  2001,  1686 
  • 5a Bagley MC. Dale JW. Merritt EA. Xiong X. Chem. Rev.  2005,  105:  685 
    Search in Google Scholar
  • 5b Bagley MC. Glover G. Merritt EA. Synlett  2007,  2459 
  • 5c Merritt EA. Bagley MC. Synlett  2007,  954 
  • 5d Bagley MC. Chapaneri K. Dale JW. Xiong X. Bower J. J. Org. Chem.  2005,  70:  1389 
    Search in Google Scholar
  • 5e Bagley MC. Xiong X. Org. Lett.  2004,  6:  3401 
    Search in Google Scholar
  • 6 Bohlmann F. Rahtz D. Chem. Ber.  1957,  90:  2265 
    CrossrefSearch in Google Scholar
  • 7 Aulakh VS. Ciufolini MA. J. Org. Chem.  2009,  74:  5750 
    Search in Google Scholar
  • 8a Kantevari S. Chary MV. Vuppalapati SVN. Tetrahedron  2007,  63:  13024 
    Search in Google Scholar
  • 8b Kantevari S. Chary MV. Vuppalapati SVN. Lingaiah N. J. Heterocycl. Chem.  2008,  1099 
  • 9a Lieby-Muller F. Allais C. Constantieux T. Rodriguez J. Chem Commun.  2008,  4207 
  • 9b Davis JM. Truong A. Hamilton AD. Org. Lett.  2005,  7:  5405 
    Search in Google Scholar
  • 9c Senaiar RS. Young DD. Deiters A. Chem. Commun.  2006,  1313 
  • 9d Alnajjar A. Abdelkhalik MM. Al-Enezi A. Elnagdi MH. Molecules  2009,  14:  68 
    Search in Google Scholar
  • 9e Riyadh SM. Abdelhamid IA. Al-Matar HM. Hilmy NM. Elnagdi MH. Heterocycles  2008,  75:  1849 
    Search in Google Scholar
  • 9f Al-Saleh B. Abdelkhalik MM. Eltoukhy AM. Elnagdi MH. J. Heterocycl. Chem.  2002,  39:  1035 
    Search in Google Scholar
  • 9g Bashford KE. Burton MB. Cameron S. Cooper AL. Hogg RD. Kane PD. MacManus DA. Matrunola CA. Moody CJ. Robertson AAB. Warne MR. Tetrahedron Lett.  2003,  44:  1627 
    Search in Google Scholar
  • 9h Omran FA. Awadi NA. Khair AAE. Elnagdi MH. Org. Prep. Proced. Int.  1997,  29:  285 
    Search in Google Scholar
  • 9i Reddy GJ. Latha D. Thirupathaiah C. Rao KS. Tetrahedron Lett.  2005,  46:  301 
    Search in Google Scholar
  • 10a Tambade PJ. Patil YP. Bhanage BM. Curr. Org. Chem.  2009,  13:  1805 
    Search in Google Scholar
  • 10b Comelles J. Moreno-Mañas M. Vallribera A. ARKIVOC  2005,  (ix):  207 
    Search in Google Scholar
  • 11a Bartoli G. Marcantoni E. Sambri L. Synlett  2003,  2101 
  • 11b Bartoli G. Fernandez-Bolanos JG. Antonio GD. Foglia G. Giuli S. Gunnella R. Mancinelli M. Marcantoni E. Paoletti M. J. Org. Chem.  2007,  72:  6029 
    Search in Google Scholar
  • 11c Khodaei MH. Khosropour AR. Kookhazadeh M. Synlett  2004,  1980 
  • 11d Christoffers J. Kauf T. Werner T. Rössle M. Eur. J. Org. Chem.  2006,  2601 
  • 12a Haines AH. Lamb AJ. Carbohydr. Res.  2000,  325:  323 
    Search in Google Scholar
  • 12b Jenkinson SF. Booth KV. Gullapalli P. Morimoto K. Izumari K. Fleet CWJ. Watkin DJ. Acta Crystallogr., Sect. E: Struct. Rep. Online  2008,  64:  o1705 
    Search in Google Scholar
  • 12c Methling K. Kopf J. Michalik M. Reinke H. Burger C. Oberender H. Peseke K. J. Carbohydr. Chem.  2003,  22:  537 
    Search in Google Scholar
13

We thank one of the referees for suggesting conjugated dihydropyridine intermediate in the mechanistic sequence in Scheme  [³] .